After the state acquired the abandoned Milwaukee railroad right of way in 1980, outdoorsman Chic Hollenbeck, a big fan of the cowboy actor and founder of John Wayne Pioneer Wagons and Riders Association, spearheaded an effort to save the right of way as a trail. The Trail owes its existance and its name to the successful lobbying campaign by the JWPWR, whose members make an annual trek along the trail by wagon and horseback. The JWPWR members also devote countless volunteer hours to trail improvements and advocacy, and are embassadors for the Trail each year on their annual ride.

Members of the John Wayne Pioneer Wagons and Riders Association outside tunnel

The Cascade Rail Foundation is dedicated to promotion and preservation of the railroad history of the Milwaukee Road through Washington, and the corridor that is now the John Wayne Pioneer Trail. The historic depot, electric substation, and old railroad yard at South Cle Elum, landmarks on the JWPT/Iron Horse State Park, were preserved through efforts of the Cascade Rail Foundation. Cascade Rail continues to support and work toward saving and improving the JWPT.

South Cle Elum station (a National Historic Landmark) restored through efforts of the Cascade Rail Foundation.

Volunteeers from John Wayne Pioneer Wagons and Riders and Cascade Rail Foundation, restoring pumphouse at Ralston station